7-Day Santorini and Astypalea Island Escape: Beaches, History, and Greek Cuisine

Day 1: Arrive and Explore Fira

Santorini, Greece on June 1, 2025

9:00am

Breakfast at Pelican Kipos

Enjoy a healthy and tasty breakfast in a charming garden setting right in Fira town center. They serve smoothies, Greek pastries, and fresh coffee to start your day energised.
EUR12, 1h0m

10:30am

Explore Fira Town and Archaeological Museum

Wander the iconic clifftop town of Fira, browsing shops and soaking in caldera views. Visit Santorini Archaeological Museum (open 8am-3pm) to discover fascinating Cycladic artifacts.
EUR6, 2h0m

1:00pm

Lunch at Naoussa Restaurant

Sample traditional Santorinian cuisine such as tomato keftedes and grilled octopus with a stunning view of the caldera.
EUR25, 1h30m

3:00pm

Cable Car Ride to Old Port

Take the famous cable car down to the Old Port for beautiful vistas and the option to take a boat cruise later.
EUR7, 30m

5:00pm

Visit Oia for Sunset

Catch a local bus or drive to Oia to witness one of the world’s most famous sunsets, perfectly lighting up the whitewashed buildings and blue domes.
Free, 2h0m

7:30pm

Dinner at Ammoudi Fish Tavern

Enjoy fresh seafood right by the water at Ammoudi Bay below Oia, a classic Santorini experience open until 11pm.
EUR30, 2h0m
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Day 2: Ancient Sites and Vineyards

Santorini, Greece on June 2, 2025

8:30am

Breakfast at Passaggio

This stylish spot in Fira offers excellent crepes and coffee, opening at 8am for a quick and delicious start to the day.
EUR15, 1h0m

9:45am

Visit Akrotiri Archaeological Site

Explore the remarkably preserved ancient Minoan volcanic settlement, known as the 'Pompeii of the Aegean'. Open 8:30am-3pm.
EUR12, 2h0m

12:00pm

Lunch at The Cave of Nikolas

Scenic taverna near Red Beach with fresh seafood and traditional Greek dishes.
EUR20, 1h30m

2:00pm

Red Beach Relaxation

Spend a couple of hours swimming and sunbathing on Santorini’s famous Red Beach, known for its towering red cliffs and crystal waters.
Free, 2h0m

4:30pm

Santorini Wine Tasting Tour

Join a guided tour to local vineyards like Santo Wines or Venetsanos Winery to sample premium Assyrtiko wines while overlooking stunning views. Tours typically run until 7pm.
EUR30, 2h0m

7:30pm

Dinner at Metaxi Mas

Popular hidden gem with authentic Cretan dishes and Santorini delicacies in a rustic setting in Exo Gonia village.
EUR28, 2h0m
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Day 3: Santorini Island Hopping

Santorini, Greece on June 3, 2025

7:30am

Breakfast at your hotel or nearby café

Start early with a simple breakfast near your accommodation in preparation for a full day.
EUR10, 0h45m

8:30am

Boat Tour to Nea Kameni Volcano and Hot Springs

Depart from the Old Port for a half day adventure hiking the volcanic island and swimming in warm natural springs (tours run 8:30am-12:30pm).
EUR40, 4h0m

1:00pm

Lunch at Pelican Kipos

Return to Fira and enjoy a relaxing lunch in the garden surroundings, perfect for unwinding after the tour.
EUR20, 1h30m

3:00pm

Visit Pyrgos Village

Drive or bus to Pyrgos, a beautiful hilltop village with panoramic island views and traditional architecture.
Free, 1h30m

5:00pm

Relax at Amoudi Bay

Head back to Oia’s Amoudi Bay for late afternoon swimming or a coffee by the water.
Free, 1h30m

7:00pm

Dinner at Petra Restaurant

Savor Mediterranean fusion dishes with sunset views in the village of Imerovigli, open until 10pm.
EUR35, 2h0m
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Day 4: Travel to Astypalea

Santorini to Astypalea, Greece on June 4, 2025

7:00am

Breakfast at your hotel

Early breakfast to prepare for travel day.
EUR10, 1h0m

8:00am

Travel from Santorini to Astypalea by ferry

High-speed ferry departs from Santorini port to Astypalea, journey takes roughly 4-5 hours so book tickets in advance.
EUR50, 5h0m

2:00pm

Check-in and Rest at Hotel

Arrive at Astypalea, check into your hotel, and relax a bit before exploring the island.
Varies, 1h30m

3:30pm

Explore Chora Village

Stroll around Astypalea's charming capital with its whitewashed houses and butterfly-shaped harbor.
Free, 2h0m

6:00pm

Dinner at Peskesi Tavern

Enjoy fresh local seafood and traditional Greek flavors with a view of the Aegean Sea.
EUR25, 2h0m
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Day 5: Beaches and History

Astypalea, Greece on June 5, 2025

8:00am

Breakfast at Archontariki Cafe

Start your day with coffee and homemade pastries popular with locals.
EUR10, 1h0m

9:00am

Visit Astypalea Castle

Explore the Venetian castle overlooking the town, open from 9am to 6pm, offering spectacular panoramic island views and historical insights.
EUR3, 2h0m

11:30am

Relax at Livadi Beach

Spend a peaceful few hours swimming and sunbathing at the sandy and easily accessible Livadi Beach.
Free, 3h0m

2:30pm

Lunch at Taverna To Delfini

Casual spot serving traditional Greek dishes near the beach, open until 4pm.
EUR20, 1h30m

4:30pm

Explore Limenaria and Agios Konstantinos

Visit two of the island’s most charming small villages for walks and coffee breaks.
Free, 2h0m

7:30pm

Dinner at Dimitris Tavern

Traditional Greek taverna famous for grilled meats and fresh salads.
EUR25, 2h0m
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Day 6: Island Adventure

Astypalea, Greece on June 6, 2025

7:30am

Breakfast at your hotel

Light breakfast before a day of adventure exploring the island.
EUR10, 0h45m

8:30am

Hire a Scooter or Jeep - Island Tour

Rent a vehicle to discover secluded beaches like Kaminakia and Vatses plus hiking routes. Rental shops open from early morning.
EUR40, 6h0m

2:30pm

Lunch Picnic at a Secluded Beach

Pack local delicacies from a market for a picnic lunch amidst pristine natural scenery.
EUR15, 1h0m

4:00pm

Return and Rest

Return vehicle and relax at your hotel or local café.
Free, 2h0m

7:00pm

Dinner at Chora's Panorama Restaurant

Dine with breathtaking views of the sunset and coastline, experiencing refined Greek cuisine.
EUR30, 2h0m
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Day 7: Departure Day

Astypalea, Greece on June 7, 2025

8:00am

Breakfast at a local bakery

Sample fresh Greek pastries and coffee as a final taste of island life.
EUR8, 1h0m

9:30am

Last stroll through Chora

Enjoy a relaxed morning walk around the quaint streets for any last minute photos or souvenirs.
Free, 1h0m

11:00am

Transfer to Port or Airport

Prepare for your departure via ferry or plane with ample time to check in.
Varies, Varies
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